If you write, underwrite, or manage risk for motor carriers, you already know the last few years have been rough. Freight recession. Rate pressure. Carriers going under. And a growing pile of headlines about unsafe operators still finding a way to get insured.
So what does it look like from the other side of the desk? What does a 40-year trucking veteran, who now chairs one of the industry’s largest carrier associations, actually think insurance professionals need to hear?
MCIEF Education Director Beverly Raiford sat down with Mark Seymour, CEO of Kriska Transportation Group and Chairman of the Truckload Carriers Association (TCA), to find out. Mark will bring that same perspective to the stage this October at the 2026 MCIEF Leadership Conference in Scottsdale, and honestly, this conversation is a preview worth reading before you register.
A Trucker First, a Chairman Second
Mark didn’t start in a boardroom. He started as an 18-year-old truck driver, working alongside his father, who founded Kriska back in 1978 with three trucks and, in Mark’s words, “extremely humble beginnings.” Forty-plus years later, Mark runs the company his dad built and chairs TCA, on top of past leadership roles with the Ontario Trucking Association and the Canadian Trucking Alliance.
That background matters here, because Mark isn’t a policy wonk or a hired spokesperson. He’s someone who has bought insurance, filed claims, and worked with risk managers for four decades. When he talks about what carriers need from insurance partners, it comes from having lived it, not from a script.
Why Should Insurance Professionals Care What a Carrier Thinks?
That’s the question Beverly put to him directly, and Mark’s answer sets the tone for the whole interview. He didn’t dodge it or soften it. His take, essentially: insurance is part of a supply chain built on accountability, and everyone in that chain, carriers included, has to keep earning trust.
“I think what we’ve all experienced through time and through the growth and maturity of our industry is whether you’re selling trucks, whether you’re lending money, whether you’re providing insurance, whether you’re training drivers, there’s a high amount of accountability and responsibility,” Mark said.
He pushed the point further, arguing that every insured company deserves a “fine-tooth comb” review before a policy gets written, not just a look at whether the premium check will clear. In his view, the real question an insurer should be asking isn’t just “can they pay,” but “does their culture, their values, and their safety record actually back up the risk we’re taking on.”
The Line That’s Going to Get Quoted
Somewhere around the midpoint of the interview, Mark shares something his late father used to say, and it’s blunt: “If you sleep with dogs, you’re bound to get fleas.”
His point wasn’t about being harsh toward carriers. It was aimed at the insurance side of the table. Mark’s question back to insurers in the room: is the due diligence process deep enough to actually know who you’re insuring? Or are some carriers getting coverage simply because they can afford the premium, regardless of their safety record?
He connects this directly to a real, current legal shift, the Montgomery case, where a third-party broker was held liable for the carrier they chose to work with. Mark thinks this kind of accountability could eventually extend further up the chain, including to insurers themselves. Whether or not that prediction comes true, it’s the exact conversation MCIEF members need to be tracking, and it’s a big reason Mark’s session is one to circle on the conference agenda.
Not About Cheapest Price, About the Right Risk
One thing Mark returns to more than once: insurance shouldn’t be a race to offer the best product at the best price to every carrier that walks in the door. In his words, it should be “the best product at the best price to those that deserve the best product at the best price. And not everybody deserves it.”
That’s a strong statement coming from a carrier CEO, not an insurance executive. Mark seems genuinely convinced that a stricter, more disciplined underwriting standard is good for the whole trucking ecosystem, safer roads, more sustainable rates for carriers actually doing things right, and less exposure for insurers holding the bag when things go wrong.
He also points to something worth sitting with: right now, some carriers are finding it harder, and more expensive, to get insured. Mark doesn’t see that as a problem. He sees it as evidence the system is starting to work the way it should.
Why He Said Yes to Scottsdale
This will be Mark’s first time attending an MCIEF Leadership Conference, and he was refreshingly candid about why he agreed to come. It’s not a paid speaking gig, and it’s not about promoting Kriska. As Mark put it, “I’m sharing space with people who care, and I’m there because I care… I’m the chairman of the Truckload Carriers Association because I care. I don’t get paid to do that either.”
He also made a point that resonates with anyone who’s ever sat through a conference and wondered if the real value was on stage or in the hallway. Mark said some of the most valuable moments happen away from the microphone, at dinner, over cocktails, in the smaller, more direct conversations with people who want to dig into specifics. That’s part of what he’s most looking forward to in Scottsdale: not just his stage conversation with TCA President Drew Easton, but the one-on-one time with the carriers, brokers, and underwriters actually in the room.
What This Means for You
If you work in trucking insurance, whether you’re underwriting fleets, managing claims, or advising carrier clients, Mark’s perspective gives you something valuable: a direct look at how a respected carrier leader thinks about risk, accountability, and what actually earns trust between carriers and their insurance partners.
That’s exactly the kind of insight MCIEF built the Leadership Conference around. Mark will be on stage with TCA President Drew Easton this October, sharing more of the fresh material he’s gathering from TCA’s officer group meeting just ahead of the event. It’s a rare chance to hear directly from a sitting association chairman, in person, and to ask him the follow-up questions this interview only had time to start.
Join Us in Scottsdale
The 2026 MCIEF Leadership Conference runs October 4 through 7 at the Grand Hyatt Scottsdale Resort. Along with Mark Seymour’s conversation with Drew Easton, the agenda includes keynote sessions, the MCIEF Top 10 Trucking Insurance Industry Issues discussion, the State of the Market Report, and plenty of built-in time for the kind of hallway and dinner-table conversations Mark says matter just as much as the main stage.
If you’re serious about growing as a leader in trucking insurance, and about hearing directly from the carrier side instead of just reading about it, this is where that conversation happens. Register for the 2026 MCIEF Leadership Conference and reserve your seat in Scottsdale this October.
Not yet an MCIEF member? Membership gets you access to events like this one, along with the TRS and TCS designation programs and year-round continuing education built specifically for trucking insurance professionals. Visit mcief.org to learn more about membership and how to get involved.